OTAs / Distribution Episodes

Send us a message! Direct booking has been part of the vacation rental conversation for years, but one challenge remains hard to solve. Travelers are not always searching that way. In this episode, Alex & Annie sit down with Eric Goldreyer, CEO and founder of Savvy, to talk about why direct booking has struggled to become a consumer habit and what needs to change for travelers to find, trust, and use it more easily. Eric shares how Savvy evolved from BNB Finder into a book-direct market...

Send us a message! In this episode of Alex & Annie: The Real Women of Vacation Rentals, we are joined by Bob Milne, President and COO of First Chair Destinations. Bob has spent decades in the vacation rental industry, with leadership experience across Steamboat Resorts, Wyndham Vacation Rentals, Vacasa, Casago, and now First Chair Destinations. His career has taken him from building a local vacation rental company in Colorado to helping lead large-scale portfolios across some of the most reco...

Send us a message! AI is changing the way travelers search, compare, and book vacation rentals. But what does that mean for direct bookings, local brands, and the websites operators have spent years building? In this episode, Alex & Annie are joined by Richard Vaughton of Yes Consulting and Mark Simpson of Boostly for The Great AI Debate. After taking this conversation to the stage at the Host Planet Roadshow in London, Richard and Mark continue the discussion around what AI could mean for va...

Send us a message! In this second episode of First of the Month Wrangle, presented by Lasoh, Alex & Annie are joined again by Orlie Benjamin, Founder and CEO of Lasoh, to continue the conversation around vacation rental marketing and what it takes to make it more effective, more personal, and more guest-centered. This time, the conversation focuses on a simple but important question: can we stop marketing properties and start marketing to people? For many vacation rental operators, marketing ...

Many vacation rental operators are working on their direct booking strategy, but the real opportunity is not just driving more traffic to their website. It is understanding what happens once guests get there. In this episode, we are joined by Chris Walker, Owner of Luxury Homes of Hilton Head and CEO of Direct Booking Tools. Chris shares what he has learned from nearly two decades in property management and how his experience as an operator led to the creation of Direct Booking Tools. T...

Send us a message! In this special episode, Alex and Annie sit down with Tim Rosolio, Vice President of Vacation Rental Partnerships at Vrbo, for a behind-the-scenes look at Vrbo’s Vacation Rentals of the Year program and what it takes to earn that recognition. Recorded on location at Lakefront Escape on Squam Lake, New Hampshire, one of this year’s winning properties, the episode offers both a platform perspective and a firsthand look at the kind of hospitality Vrbo is celebrating. Tim sh...

Send us a message! We’re kicking off a new special series, First of the Month Wrangle, in partnership with Lasoh, where we’ll dig into the strategies, systems, and blind spots shaping one of the most important and often misunderstood areas of vacation rentals: marketing. Throughout the series, Alex & Annie will be joined by Orlie Benjamin, Founder and CEO of Lasoh, a vacation rental marketing platform built to help operators drive more direct bookings and increase profit through deeper relati...

Send us a message! Distribution in the vacation rental industry has never been more complex. Property managers today are balancing major OTAs, niche platforms, emerging luxury channels, and an increasingly layered tech stack, all while trying to deliver exceptional guest experiences. In this episode, Alex & Annie sit down with Blake Warner, CEO of BookingPal, to talk about how distribution is evolving and what it takes to build scalable infrastructure in a rapidly maturing industry. Blake ...

Send us a message! Midterm rentals are moving from a side option to a real strategy. In this episode, Alex & Annie sit down with Jeff Hurst, CEO of Furnished Finder and former HomeAway and Expedia Group leader, to explain why 30+ day stays are gaining traction as many STR markets move into a more mature phase. Jeff breaks down what makes midterm rentals different from short-term rentals, what demand is actually driven by, and why midterm can be a strong fit for operators looking for stability, ...

Send us a message! Condo-hotels and resort-style properties sit in a tricky middle ground. They are not traditional hotels, but they are not quite vacation rentals either. Many still run on hotel tech stacks, charge hotel-style commissions, and operate with hotel mindsets. Meanwhile, guests are increasingly searching on vacation rental channels, homeowners are asking why they cannot find their units online, and off-site managers charging half the commission are pulling inventory away. In ou...

Send us a message! VRMA International 2025 is in the books and if you were there, you probably felt it too: this year hit differently. More people, deeper conversations, and a sense that the vacation rental industry is entering a new chapter. But what actually stuck after the applause faded? In this episode, Alex & Annie sit down with Tim Rosolio, Ela Mezhiborsky, and Jessica Gillingham to reflect on what stood out most, not just from the sessions, but from the conversations around the show. ...

Send us a message! When Airbnb changes its policies, the ripple effect can shake operators everywhere. For many, the problem is deeper than one policy update. Relying too heavily on a single platform leaves businesses vulnerable, and the cracks are starting to show. In this episode, Mark Simpson, CEO and founder of Boostly, shares why now is the time for vacation rental operators to double down on direct bookings. Drawing from more than a decade of helping hosts grow beyond OTAs, Mark brings ...

Send us a message! Airbnb’s evolving policies have become one of the most pressing conversations in vacation rentals today - sparking questions, frustrations, and new realities for property managers across the industry. In this episode, Alex & Annie welcome Dennis Schaal, Founding Editor at Skift, to unpack what these changes really mean for property managers, and the broader short-term rental ecosystem. With more than 25 years of experience covering online travel, Dennis brings a sharp journ...

Send us a message! This week, we’re joined by Deborah Labi, a seasoned hospitality professional and the founder of Have You Got, a verified global guest referral network designed to help independent property managers expand their reach and maximize revenue without sacrificing the personal touch that sets them apart. With two decades of experience in the industry, Deborah understands the frustration of turning away great guests, whether due to lack of availability or location. That challenge led...

Send us a message! Many short-term rental operators think that getting listed on Airbnb or Vrbo is enough. But in today’s competitive landscape, basic distribution is no longer enough to stand out or to sustain growth. In this episode, we’re joined by Lennart Kok, VP of Distribution and Marketing at NextPax, to explore what smarter vacation rental distribution really looks like. With a background at Hilton, Booking.com, and now NextPax, Lennart brings rare insight into where distribution ofte...

Send us a message! What happens when one of the world’s most trusted hotel brands steps into the vacation rental space? In this episode, we’re joined by Jane Gavin (Senior Director of Brand Marketing & Guest Experience) and Keven Wishard (Senior Director of Global & Continent Operations) from Homes & Villas by Marriott Bonvoy. With decades of hospitality experience between them, Jane and Keven take us inside Homes & Villas by Marriott Bonvoy’s bold approach to short-term rentals. One built...

Send us a message! In this episode of Alex & Annie: The Real Women of Vacation Rentals, we’re joined by Ian Ackland, Managing Director of the Americas at Booking.com, for a candid look at how one of the world's largest travel platforms is evolving its approach to better serve property managers. With more than 30 years in the travel industry and over a decade at Booking.com, Ian shares how the company is shifting from being just a distribution channel to becoming a true partner for vacation rent...

Send us a message! In this episode of Alex & Annie: The Real Women of Vacation Rentals, we sit down with Tim Rosolio, Vice President of Vacation Rental Partnerships at Expedia Group, to discuss VRBO’s vision for 2025 and beyond. Tim shares insights on VRBO’s evolving strategy, including how the platform has transformed since its transition from HomeAway, its commitment to professional property managers, and its focus on delivering exceptional guest experiences. He also provides an inside look...

In this week’s episode, we are thrilled to welcome back Terry Whyte, owner of Anna Maria Island Beach Rentals and a renowned expert in vacation rental technology and operations. As one of the leading voices in the vacation rental industry, Terry dives into the evolving landscape of vacation rental software, sharing his predictions and practical insights on what’s driving innovation in the field. From the rise of "all-in-one" solutions to the growing dominance of CRM platforms, this episode sh...

This week, we’re thrilled to welcome back John Hildebrand, founder of Hilde Homes and a leading advocate in the short-term rental industry. From his early days as a property manager to becoming a leading voice in vacation rental advocacy and education, John shares his inspiring journey with authenticity, humor, and valuable insights. With firsthand experience navigating the challenges of hosting, John highlights the vital role of advocacy in driving positive change for operators, guests, and ...

This week, we’re coming to you live from the heart of Florence, Italy, where Alex & Annie attended Scale Italia 2024! In this special on-the-ground episode, we bring you a dynamic mash-up of conversations with some of the most influential figures in the vacation rental and property management industries. Hear firsthand perspectives from Italy’s vibrant conference floor, where the future of global property management, tech trends, and regulatory changes in the short-term rental space were top of ...

Exclusive offer for Alex & Annie listeners: Get $400 off your onboarding fee when you partner with Hostaway using this link: ⁠http://get.hostaway.com/alexandannie In this episode, we sit down with Zach Busekrus, Founder/CEO of StayWatch and host of the "Behind the Stays" podcast. Zach shares his unique journey into the short-term rental industry, from living exclusively in Airbnbs during the pandemic to founding a company that's revolutionizing how travelers find and book vacation rentals. ...

Exclusive offer for Alex & Annie listeners: Get $400 off your onboarding fee when you partner with Hostaway using this link: http://get.hostaway.com/alexandannie Welcome to our August 1st of the month bonus episode! Today, we welcome back Simon Lehmann, a seasoned expert in the vacation rental industry and the co-founder and CEO of AJL Atelier. With over two decades of experience, Simon has been at the forefront of innovation and strategy, guiding countless property management companies throu...

Exclusive offer for Alex & Annie listeners: Get $400 off your onboarding fee when you partner with Hostaway using this link: http://get.hostaway.com/alexandannie In this episode, Alex and Annie are joined by Eric Goldreyer, the CEO and owner of BnBFinder. Eric shares his journey in the bed and breakfast and vacation rental industry, discussing his previous ventures and how they led to the creation and success of BnBFinder. He also talks about the challenges and opportunities within the ind...